Nice Guys Get the Girl
by Becks Rylynn
Summary: A blow to the head turns Dean into a regular gentleman. Especially around Ruby. OR: The evolution of Dean and Ruby's relationship as seen through Sam's eyes. For Amanda's birthday!


_AN: Happy Birthday, Amanda!_

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**Title:**_ Nice Guys Get the Girl  
_**Summary:** Season three fic: A blow to the head turns Dean into a regular gentleman. Especially around Ruby. OR: The evolution of Dean and Ruby's relationship as seen through Sam's eyes.  
**Pairing:** Dean/Ruby, Sam/Ruby friendship, Dean/Sam brotherly awesomeness.  
**Genre:** Humor/Romance. With a healthy dose of the above mentioned Dean/Sam brotherly goodness.  
**Rating:** T for a few curses.  
**Timeline:** Season three.  
**Spoilers:** General spoilers for season three.  
**Warnings:** This story is pure crack and fluff. It's crackfluff. Fluffycrack. So beware, there's...you know...fluff and crack ahead.  
**Dedication:** To** Daddy's LiL Heartbreaker **on her birthday! Because she loves D/R and she adores Sam. Happy Birthday, friend of mine!

**Disclaimer: **I do not own anything.

* * *

**Nice Guys Get the Girl**

_Written by Becks Rylynn_

* * *

_For Amanda's Birthday_

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Taking a nasty blow to the head was nothing new for a Winchester.

To be perfectly frank, Sam was surprised he and Dean hadn't dropped dead of a brain hemorrhage or something to that affect. Apparently, Winchester men had hard heads. He was grateful for that. Did their thick headedness make seeing his brother get thrown head first into a tombstone any less terrifying and gut wrenching? No, not really.

Dean went limp like a rag doll and Sam's heart sank into his stomach like a stone. ''Dean!''

There was a groan and the limp body on the ground twitched. ''Burn the damn bones!'' Was thrown back at him and Sam tossed the match onto the bones without a second of hesitation. The homicidal ghost who liked to throw people went bye-bye, Dean got up and Sam made the mistake of thinking everything was fine. Because everything looked fine. Other than looking annoyed and rubbing at his head, Dean looked fine.

''You all right?'' Sam asked, brushing dirt off his jeans.

''Fine,'' Dean grumbled.

He appeared to be shaking off the blow as they were trudging back to the car and yeah, maybe it was a little odd that he tossed Sam the keys to the car, but lately Dean had been letting him drive a lot more. ''You're gonna have to get used to driving her,'' Dean always said. ''And she's gonna have to get used to letting you drive her,'' was usually added on, making Dean sound just a tad crazy. Dean had been doing a lot of stuff he didn't normally do lately as if to say, _Sorry you'll have to live with the guilt that I did all of this for you._

But really, Sam thought everything was fine.

Dean seemed perfectly okie dokie.

At first.

* * *

Later, as they were approaching an all night diner with Sam jingling the keys in his hand (he was, admittedly, a little surprised Dean hadn't asked for them back yet) and Dean whistling something that had an undeniable Disney-esque quality to it, she came out of the shadows.

It seriously freaked Sam out. One minute they were alone in the parking lot and the next, she was stepping out from behind a blue pickup truck, greeting them with a smooth ''Hello, boys.'' He yelped and dropped the keys. Dean stopped whistling. Ruby smirked in Sam's direction, shaking her head as she watched him pluck the keys from the cold pavement. ''Wow,'' she drawled. ''You truly are unshakable.''

Sam scowled. ''Can it.''

But the really freaky part came when Dean's eyes positively lit up and a wide grin stretched across his lips. ''Hi, Ruby,'' he greeted. ''How are you? You look nice tonight.''

It clearly threw everything off. Sam swore he felt the world tip on its axis.

Blinking, obviously taken aback by Dean's uncharacteristic politeness towards _her_ of all people, Ruby's lips parted and all that came out was an actual honest to God squeak. ''I...'' She cleared her throat and avoided his eyes, wrapping her arms around her middle. Sam was torn between the strangeness of Dean's sudden change of heart towards Ruby and the equal oddness of how easy it was for Dean to make Ruby uncomfortable. _Fascinating_. After a moment of silently studying him, Ruby pursed her lips, narrowed her eyes and leaned closer to Dean. ''Is this a game?''

He smiled pleasantly and leaned even closer so that their faces were too close for even Sam's comfort. ''Would you like it to be?''

Sam's eyebrows shot into his hairline.

Looking like she was growing increasingly flustered, Ruby reared back and wound up stumbling. When Sam saw how wide her eyes were and how speedy her breathing was, he had to wonder if her reaction was shock or...possibly something else.

It was only when Dean actually held the door open for her and she spent the next minute trying unsuccessfully to come up with something acceptable to say that Sam finally decided Ruby may have been a badass demon, but she had a bit of a spastic side.

* * *

''So, what are you doing here?'' Sam questioned, keeping an eye on Dean who in turn, was keeping an eye on Ruby...for reasons Sam still did not understand.

Ruby shrugged and by the way her hands were clenched tightly, Sam could easily tell both Dean's gaze and his proximity to her was beginning (or continuing) to unnerve her. He was having the hardest time resisting the urge to tell her that she was the one who _chose _to sit next to Dean. ''I caught wind of a werewolf problem down in Louisiana. Thought I'd give you two something to do.''

''You have very beautiful eyes, you know.''

Sam choked on the bitter coffee that was now stinging his throat and Ruby's eyes widened as they both slowly looked at Dean. ''W-What?'' Ruby stuttered out at last, drawing herself away from Dean. When their shoulders brushed, she stiffened and couldn't look at him.

Sam couldn't decide if this was amusing or head scratching. The obvious reason for this sudden change in Dean's behavior towards the blonde was alcohol. It was entirely possible that he had somehow managed to persuade the waitress to put a little something extra in his coffee. Dean had always had a way with waitresses, after all. Another reason would be Dean deliberately trying to piss Ruby odd and settling for flustering her instead. Whatever Dean's master plan was, Sam was sure it wasn't going to end well.

''What?'' Dean frowned. ''Why are you looking at me like that?''

''What did you just say?'' Ruby demanded.

He tilted his head to the side. ''When?''

''Dean!''

''What?'' He paused, blinked and looked at her closely. ''Your eyes are beautiful,'' he pointed out matter-of-factly, like it was the first time he had made this observation. ''Very...blue. Clearly your most prominent feature.''

She scoffed and looked away from him. ''You mean like yours?'' She said it in a mumble, but both Winchesters heard it loud and clear and when she realized what she just said, her eyes widened and she went to great lengths to avoid Dean's eyes. Sam watched them both with interest, all attempts to figure out Dean's end game failing horribly.

Dean on the other hand, grinned and leaned his elbow on the table, resting his head in the palm of his hand. ''You think my eyes are my most prominent feature?''

''No, I just...'' She trailed off, grasping for something to say. Even Sam felt a smirk tugging at the corner of his mouth. It was extremely amusing to see super composed Ruby all flustered and this close to blushing. ''Shut up,'' she got out, stealing Dean's untouched coffee with a scowl.

''Do you know what I think?'' He asked conversationally, sitting up straight and looking at Ruby with a smile. When she jerked and her knee hit the table, effectively sending coffee sloshing over the rims of the cups on the table, it was enough to tell Sam that his brother had just put his hand on her knee. Dear God, was Dean actually trying to put the moves on Ruby? Was he aware she was going to beat him down into bloody pulp? ''I think we should bond. I don't know why we haven't.''

Ruby stared at him for several seconds before glaring and punching him on the shoulder. ''I don't know what you're trying to do, Dean - ''

''What are you talking about?''

''This!''

''What?''

''Your attitude.''

''I'm just being polite.''

''Exactly!'' She all but staggered out of the seat, glaring down at Dean like he was a piece of dirt. Or at least that was probably what she was going for. She looked more flushed than anything else. Honestly, Sam didn't think she was vehemently disliking this as much as she was obviously trying to. ''Why?'' She growled out. ''Why would you want to be nice to me?''

Dean shrugged. ''I don't know. 'Cause you're hot?''

Sam swung his gaze from Dean to Ruby. Even she couldn't hide the tiny, brief smile that flickered on her lips. It was gone in an instant, but Sam knew what he saw. She was liking this, wasn't she? Dean really could charm anyone he wanted to. ''Okay,'' Ruby said slowly, eyeing Dean wearily. ''Raise your hand if disturbed.''

Dude, this whole thing was disturbing.

Before he even realized what he was doing, Sam began to raise his hand, only to stop and clear his throat when he remembered it was a stupid thing to do.

''Why is this so weird?'' Dean burst out, throwing his hands up. ''I'm not acting any different.'' He rose to his feet to tower over Ruby and when he stumbled and absently brought a hand up to rub the back of his head, the alarm bells that had been ringing in warning suddenly went off in high volume. ''You know what I think?'' Dean asked, staring down at Ruby.

There was a moment of prolonged silence and then Ruby spoke up. ''What?'' Sam could practically see the tiny webs of concern spinning through her eyes. ''What were you going to say?''

''...I wasn't going to say anything.''

''Oh,'' Ruby smirked and crossed her arms, but Sam thought she looked a little anxious. ''Suddenly this is all making sense.''

''Oh my _GOD_!'' Sam yelped, leaping to his feet and pointing an accusing finger in his brother's direction. ''You have a concussion!''

''I do not,'' Dean snapped irritably. ''And why are you talking so loud?''

''I knew you weren't fine.''

''Fine,'' Dean parroted. ''I'm _always_ fine, little brother. Why wouldn't I be?''

''Dean, you were thrown headfirst into a tombstone.''

''I was not. ...Was I?''

''Well, this is good to know,'' Ruby nodded, latching onto Dean's arm and dragging him towards the door. ''It takes a head injury for you to be a nice guy.''

* * *

''You're pretty.''

Sam sighed impatiently when he heard his brother's ever so slightly slurred speech behind him. He fidgeted impatiently, waiting for the man with the bleeding hand in front of him to move out of the way so he could talk to Irena, the already extremely unhelpful and cranky night nurse. The waiting room was impossibly crowded (only a Winchester would need a hospital on the night of a five car pile up), Dean was looking more and more worn out with every passing second and Sam was trying to handle his panic in a productive way.

Behind him, Ruby huffed impatiently and kept her grip on Dean's arm, throwing back a ''thanks'' at Dean through gritted teeth.

''Am I supposed to hate you?'' Dean asked curiously.

''Yes,'' she deadpanned.

''Why?''

''Because I'm a demon.''

''Oh. That's a good reason. ...So how come I don't hate you?''

Sam threw a glance over his shoulder and watched as Ruby swiveled around to face Dean. She stared at him for a long time before she focused her gaze on the wall, crossed her legs and folded her arms. ''Because you have a concussion,'' she said dully. ''You're not thinking clearly.''

''Hmm,'' Dean frowned and seemed to disagree with her assessment, leaning closer to breathe on her neck. ''I feel clear.''

When the person in front of him moved away, tearing Sam out of his observation, he rushed forwards. The nurse behind the desk, however, was another story. She did not look at all happy to see him. ''Sir,'' she sighed. ''As I have told you twice now, your brother will be taken in to see the doctor as soon as - ''

''Okay, you don't seem to be getting the seriousness of this situation, Irena. My brother has a concussion! His brain could be swelling, it could be bleeding, he could hemorrhage and die! That's a bad thing!''

She pinched her lips together. ''You don't say.''

''He could die! Do you want that on your conscience? Do you? Hmm?''

She looked at him for a very long time and he was about five seconds away from breaking under her unflinching gaze when she decided to avert her eyes. ''I'll see what I can do,'' she said tensely.

Because he was growing mildly afraid of her, he simply sighed, nodded and turned back around to his brother who was, again, complimenting Ruby on her shiny hair. Apparently, a thump on the head did what exuberant amounts of alcohol usually did. Ruby looked a little less flustered from before, but that didn't stop her from hesitating a moment before she smacking his hand away from her hair.

''Sam,'' Dean spoke as soon as Sam had slumped into the seat across from them. ''Why are we here?''

Sam sucked in a breath and pinched the bridge of his nose.

''You got hurt, Dean,'' Ruby cut in, voice oddly soft. ''You have a concussion.''

He frowned. ''I do?'' His face screwed up in confusion for about half a minute and then he grinned and leaned over to whisper in her ear. ''That's okay. That just means you get to play nurse.''

She sunk farther into her seat like she was waiting for the world to swallow her whole and save her from this embarrassment. Well, she could roll her eyes and scoff all she wanted. It didn't change the fact that she was here. Sitting next to Dean. While he sloppily flirted with her. And played with her hair. Pretty darn telling, don't you think?

Sam's fingers, tapping mindlessly on the armrest of the uncomfortable waiting room chair he was sitting in, stilled when someone tapped him on the shoulder. He turned around to face Irena, whose gaze was flitting back and forth between Sam and Dean, who was now killing time by playing with the sleeve of Ruby's jacket. ''The doctor will see your brother now,'' she said shortly.

While Sam breathed a sigh of relief, Dean paled drastically and turned to face Ruby with wide, stricken eyes. ''Come with me,'' he all but pleaded, gripping her hand.

''Don't hold my hand,'' she snapped impatiently.

''Ruby...''

''Dean...'' She chuckled under her breath and shook her head. When Dean did not appear to find the humor in the situation, she sobered and blinked rapidly. ''Oh, you were serious?''

Sam arched an eyebrow. He couldn't remember Dean being this afraid of a doctor since he was ten years old and had to get his appendix removed. ''Would you just do it?'' He snapped, hauling Dean to his feet. ''The man has a concussion, all right?''

''I have a concussion?''

''Now is not the time to be a bitch.''

Ruby scowled at him and for a second there, she was almost scarier than Irena. Sam swore he saw his life flash before his eyes. Eventually, she dragged herself to her feet, sighed like she had the weight of the world on her shoulders and couldn't hide the way her lips twitch when Dean beamed at her. ''Fine, whatever. It's not like I've got anything better to do tonight.''

''I don't doubt that,'' Sam muttered.

''God, Sam.'' Dean rolled his eyes. ''Don't be such a little bitch.'' And then he held his arm out for Ruby to take.

At this point, it was only a little disturbing when, after a pause, she took it. 'Cause hey, it wasn't like this night could get any weirder.

* * *

Sometime in between the doctor checking out Dean's head and Sam falling asleep in a waiting room chair with his head tilted backwards, resulting in a sore neck when he woke up, Ruby disappeared into the night because she just had to have the dramatic entrances and exits, didn't she?

Dean may or may not have pouted a little.

* * *

Apparently, the weirdness did not stop at that night. If anything, things only got weirder.

* * *

A week after the incident, Ruby slid into a seat next to Sam and looked at Dean across the table. ''You feeling better, princess?''

Dean didn't even bother to look up from the newspaper he was reading in hopes of finding a case. ''Shut up.''

''What an original comeback, wise ass.''

''Look,'' Dean abruptly shoved the newspaper away roughly. It knocked over the ketchup bottle which Sam quickly righted and Ruby then stole, picking at the fries on Sam's plate. ''We will never speak of anything that happened that night ever again. Got it?''

''Fine,'' she shrugged carelessly. But then she smirked and met Dean's eyes. ''Do you still think I'm pretty?''

Dean tensed, opened his mouth to retort and then shook his head, grabbing the newspaper. It was painfully obvious he was only pretending to read this time. Mostly because the newspaper was now upside down. Slowly, Sam watched as Dean's lips curved into a smile and Ruby ducked her head to hide a smile of her own.

And Sam was left feeling like he had just witnessed the beginning of something that could potentially be epic.

* * *

Two weeks after that, Sam walked into a bar and stopped short when he saw Dean chatting up a blonde at the bar. That was not really anything new. But then the blonde turned her head and holy crap it was _Ruby_. And then they laughed. Dean and Ruby _laughed_. _With_ each other and not _at_ each other. And neither one of them had a concussion.

It was mind blowing.

* * *

A few days after witnessing their kinda lame attempts to flirt, Ruby saved them from a homicidal demon who was ready to throw Sam down the stairs and Dean out the window. When the demon's body dropped to the ground and she stood in his place with her knife in her hand, much like the first time Sam had set eyes on her, the first thing she did was smirk.

''See,'' she said. ''This is why you boys need me so badly.'' She cut off Sam's attempt at a retort by turning her eyes to Dean, cocky smirk shifting into a grin. ''Hi, Dean.''

Still rubbing his sore shoulder, Dean paused long enough to grin back. ''Hi, Ruby.''

Sam looked in between them and when their eye contact lasted just a moment too long, he began to feel just a tad uncomfortable. He really did not want to see his brother and Ruby eye sexing each other. That was just _unwanted._

_

* * *

_

Eventually, these isolated incidents became less isolated, more frequent and soon, they also lost the shock factor. When Sam walked into another bar and spied Dean teaching Ruby how to play pool, both laughing just a little too hard to play the game, he just rolled his eyes and ordered a beer. When he made food runs, suddenly there were two people none to gently reminding him that he couldn't forget the pie _or_ the french fries. When he walked into a diner and found Dean and Ruby absently trading sections of the newspaper without even looking at each other, looking like the picture of perfect domestication, it was no longer mind boggling.

* * *

All of those things were the precise reasons why he should not have been surprised when this happened:

He was walking up the stairs of the latest motel talking to Bobby about a case like it was any normal day. And then he opened the door to the motel room. ''Hey, Dean are you ever - OH MY GOD!'' Horror shot through him like a rocket and he staggered backwards, hands flying to his eyes as he slammed the door shut and nearly bowled Bobby over. ''CAN'T UNSEE IT! CAN'T UNSEE IT!''

''Yeah,'' Bobby grimaced and shoved his hands into his pockets, bouncing on the balls of his feet. ''I walked in on them doing that in my bathroom last week. I swear, they're like teenagers.''

''YOU KNEW?'' Sam bellowed. ''Oh, _god_,'' he moaned. ''My EYES!'' When the door opened and Dean and Ruby stumbled out with Dean's shirt buttoned wrong and Ruby hastily fixing her hair and smoothing down her own clothes, Sam gasped dramatically and pointed a finger at them. ''You were...You were DOING IT! You were having sex! You were,'' he looked around and leaned closer to them, eyes widened in scandal. ''You were_ fornicating_.''

''And you should really learn how to lock a door,'' Bobby tacked on.

Ruby looked up from fixing Dean's shirt just long enough to frown at Sam. She looked entirely unconcerned about this whole situation, which Sam found annoying. If he was caught pounding his significant other like a piece of hamburger meat, he would at least have the decency to be embarrassed. Dean and Ruby just seemed like they really wanted to get back to what they were doing. ''Oh, come on, Sam,'' Ruby drawled. ''Does this really shock you?''

''No, what shocks me is that _you_ were the one on top,'' Sam sneered sarcastically. ''Yes, this shocks me!''

''Well, actually,'' Dean brightened and reached out to pat Sam on the shoulder. ''If it makes you feel better, we take turns being on top.''

Sam was sure he looked so horrified that the others must have thought he was going to burst into tears at any given moment. ''I don't want you to talk anymore,'' he whimpered out, shaking his head and blinking rapidly to get_ that _image out of his head.

Dean shrugged in response.

''Are you really shocked by this turn of events?'' Bobby spoke up doubtfully. ''They've been dancing around each other for weeks now, Sam. Even _I _could see that.''

''Well...I...'' Sam trailed off and shuffled uncomfortably. Okay, so in retrospect, this wasn't a huge surprise. But it was still an incredibly unpleasant thing to witness. ''I guess it's not that big of a surprise. Just...when did this...start? _Why_ did this start? What exactly is _this_?''

''Whoa,'' Dean held up a hand. ''Slow down, Samantha.''

''It really only started because I wanted to see if he'd be as good as he clearly thought he was,'' Ruby answered with a smirk.

Dean shot her a look. ''Okay, I feel like you're objectifying me.''

''Oh, I totally am.''

''And strangely, I'm okay with that.''

''But after awhile,'' Ruby continued like the recent exchange did not just happen. ''It stopped being about doing it just to see if we could do it and started being about just doing it.''

''Huh,'' Sam arched an eyebrow. ''That either sounded really gross or...kind of sweet. In a weird way.''

''Then I must have told it wrong,'' she said tonelessly. ''We're not sweet.''

''Oh, I don't know about that.'' Dean smirked and draped an arm around her shoulders, pulling her to him. ''I think you're sweet.''

''I'm _not_ sweet,'' she insisted, pushing at his chest.

He chuckled and held her tighter. ''You're my _sweet_heart. Heh. Get it?''

''You're a moron. _Get it_?''

''All right,'' Sam shook his head, allowing a grimace to slip over his lips. ''Getting nauseating now. Look,'' he sighed and looked in between his brother and his brother's new...girlfriend? friend? booty call?...for a moment before rolling his eyes. ''I don't care if you're together or friends with benefits or what, I just care about my precious eyeballs, okay? Next time lock the door. Now if you'll excuse me, I have to go _wash my eyes._'' With one last shake of his head, he pushed past them and entered the room, shutting the door behind him.

Once he was gone, Bobby whistled, crossed his arms and leveled his eyes with theirs. ''What ever happened to breaking it _gently_?''

* * *

Sam Winchester was an honest man. ...Most of the time.

At first, he _honestly_ thought whatever was going on between Dean and Ruby would fizzle out impossibly quickly. Neither one of them were big on commitment, after all. But two and half months later, they were still together with no end in sight and Sam was certain that they were actually something special.

At the start of a rare hunt that Ruby wasn't tagging along on, Sam watched from the passenger seat of the Impala as Dean ran a hand down Ruby's arm, said something to her that made her smile and laugh and then pressed a kiss to the side of her head with her hand loosely grasping his jacket. It was a fairly simple gesture, but there was something undeniably intimate about it that made Sam feel like he was intruding somehow.

Eventually, after Dean tore himself away from Ruby, the driver's side door creaked open and the elder Winchester climbed in, humming under his breath. Sam studied him for a moment, easily noticing the subtle changes in his brother. Green eyes sparkled like they hadn't in a long time, his smiles were wider, he was humming and he had an almost goddamned spring in his step. Hell, even his posture was better. It was like he didn't have the weight of the world on his shoulders anymore. Like he wasn't going to die in a few months. (Sam had no idea how Ruby was going to take_ that_, but he didn't really want to think about it.) And it was all because of, as strange as it sounded, Ruby.

''You know,'' Sam mused once they were driving down the highway. ''I don't think I've seen you this happy in a long time.''

Dean stopped humming Zeppelin and flicked his eyes to his brother momentarily before shrugging, unconcerned. ''Huh. Imagine that.''

Sam smiled softly and kept his eyes on the trees outside the window. ''You love her, don't you?''

Dean's eyes widened comically and he turned to gape at Sam briefly. ''What? _Love_ her? I...No! ...I don't know. ...Maybe. I just...Hey! No chick flick moments, bitch!''

''Sorry,'' Sam apologized half heartedly. ''...Jerk.'' He shrugged. ''But you do. I know you do. I can see it in your eyes.''

Dean didn't say anything for a very long time, fingers curled tightly around the steering wheel. But then he smiled lightly, slow and genuine, before clearing his throat and trying to appear disinterested. ''So what if I do?''

Sam blinked, tilted his head to the side and then smiled, settling back against the seat. ''Maybe you should get hit on the head more often.''

Dean smirked at that, chuckle slipping through his lips. ''Somehow, I don't see that becoming a problem.''

And then Dean reached over, flipped on the radio and Metallica screamed through the confined space as the Impala rolled down the open road.

**end**


End file.
